2,3-dihydroxybutanedioic acid methyl (1R,9R,10S,11S,12R,19R)-11-(acetyloxy)-12-ethyl-4-[(12S,14R)-16-ethyl-12-(methoxycarbonyl)-1,10-diazatetracyclo[12.3.1.03,11.04,9]octadeca-3(11),4,6,8,15-pentaen-12-yl]-10-hydroxy-5-methoxy-8-methyl-8,16-diazapentacyclo[10.6.1.01,9.02,7.016,19]nonadeca-2(7),3,5,13-tetraene-10-carboxylate

• ChemBase ID: 179514
• Molecular Formular: C49H60N4O14
• Molecular Mass: 929.0191
• Monoisotopic Mass: 928.41060262
• SMILES: c1cc2c(cc1)c1c([nH]2)[C@@](C[C@H]2CN(C1)CC(=C2)CC)(C(=O)OC)c1cc2[C@@]34[C@H]([C@@]([C@H]([C@]5([C@@H]3N(CC=C5)CC4)CC)OC(=O)C)(O)C(=O)OC)N(c2cc1OC)C.C(C(O)C(=O)O)(O)C(=O)O
• Canonical SMILES: OC(=O)C(C(C(=O)O)O)O.CCC1=C[C@@H]2CN(C1)Cc1c3ccccc3[nH]c1[C@@](C2)(C(=O)OC)c1cc2c(cc1OC)N([C@@H]1[C@@]32CCN2[C@H]3[C@@](CC)(C=CC2)[C@@H]([C@]1(O)C(=O)OC)OC(=O)C)C
• InChI: InChI=1S/C45H54N4O8.C4H6O6/c1-8-27-19-28-22-44(40(51)55-6,36-30(25-48(23-27)24-28)29-13-10-11-14-33(29)46-36)32-20-31-34(21-35(32)54-5)47(4)38-43(31)16-18-49-17-12-15-42(9-2,37(43)49)39(57-26(3)50)45(38,53)41(52)56-7;5-1(3(7)8)2(6)4(9)10/h10-15,19-21,28,37-39,46,53H,8-9,16-18,22-25H2,1-7H3;1-2,5-6H,(H,7,8)(H,9,10)/t28?,37-,38+,39-,42+,43+,44-,45-;/m0./s1
• InChIKey: UUHYRRXICWUZHW-JTGGFOEZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2,3-dihydroxybutanedioic acid methyl (1R,9R,10S,11S,12R,19R)-11-(acetyloxy)-12-ethyl-4-[(12S,14R)-16-ethyl-12-(methoxycarbonyl)-1,10-diazatetracyclo[12.3.1.0^3,^1^1.0^4,^9]octadeca-3(11),4,6,8,15-pentaen-12-yl]-10-hydroxy-5-methoxy-8-methyl-8,16-diazapentacyclo[10.6.1.0^1,^9.0^2,^7.0^1^6,^1^9]nonadeca-2(7),3,5,13-tetraene-10-carboxylate
• IUPAC Traditional name: (.+-.)-tartaric acid methyl (1R,9R,10S,11S,12R,19R)-11-(acetyloxy)-12-ethyl-4-[(1R,12S,14R)-16-ethyl-12-(methoxycarbonyl)-1,10-diazatetracyclo[12.3.1.0^3,^1^1.0^4,^9]octadeca-3(11),4,6,8,15-pentaen-12-yl]-10-hydroxy-5-methoxy-8-methyl-8,16-diazapentacyclo[10.6.1.0^1,^9.0^2,^7.0^1^6,^1^9]nonadeca-2(7),3,5,13-tetraene-10-carboxylate
• Synonyms: 3',4'-Didehydro-4'-deoxy-C'-norvincaleukoblastine Ditartrate; Nor-5'-anhydrovinblastine Ditartrate; Eunades; Navelbine; Vinorelbine Ditartrate

Database IDs

• CAS Number: 125317-39-7
• PubChem SID: 164235424
• PubChem CID: 71752960

CALCULATED PROPERTIES

• Acid pKa: 10.868411
• H Acceptors: 8
• H Donor: 2
• LogD (pH = 5.5): -0.86895776
• LogD (pH = 7.4): 2.6344895
• Log P: 4.6482043
• Molar Refractivity: 216.9875 cm^3
• Polarizability: 85.129105 Å^3
• Polar Surface Area: 133.87 Å^2
• Rotatable Bonds: 13
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: White to Off-White Solid
• Melting Point: >150°C (dec.)

Safety Information

• Storage Condition: Amber Vial, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - V315000

An antineoplastic.

REFERENCES

• Curran, M.P., et al.: Drugs Aging., 19, 695 (1985)
• Mathe, G., et al.: Cancer Letters, 27, 285 (1985)
• Levegue, D., et al.: Clin. Pharmacokinet., 31, 184 (1985)